Dicyanoimidazole compounds usable as colorants for magenta toners, colored resins, colored molded resin memers and color filters

ABSTRACT

(1) Dicyanoimidazole compound derivative represented by the formula [I] ##STR1## R 1 , R 2  : alkyl group, alkoxyalkyl group, hydroxyalkyl group, β-cyanoethyl group, β-chloroethyl group, aralkyl group, aryl group; X: hydrogen atom, lower alkoxy group, methyl group, halogen atom; Y: hydrogen atom, methyl group, methoxy group, formylamino group, alkylcarbonylamino group, alkylsulfonylamino group, alkoxycarbonylamino group; --Q--: --(CR 2 ) n  -- [n: integer of 1 to 12, R: hydrogen atom, alkyl group], ##STR2## --CH═CH--, --CH 2  CH═CHCH 2  --, --CH 2  --CH═CH--]. (2) Magenta toner for color electrophotography containing at least one kind of the dicyanoimidazole compound derivative represented by the formula [I] as a coloring agent. 
     (3) Colored resin and resin color filter containing at least one kind of the dicyanoimidazole compound derivative represented by the formula [I] in solution. 
     (4) Colored molded resin member and resin color filter dyed with at least one kind of the dicyanoimidazole compound.

This is a division of application Ser. No. 07/649,759 filed Feb. 1, 1991now U.S. Pat. No. 5,233,028.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a dicyanoimidazole compound derivativeand a magenta toner for color electrophotography, colored resin, coloredmolded resin member and a resin color filter incorporating thedicyanoimidazole compound derivative.

2. Description of the Prior Art

To impart a color to toners for color electrophotography, thermoplasticresins, thermosetting resins, color filters, etc., various pigments anddyes are used according to respective uses and purposes.

For example, organic pigments are commonly utilized since they areexcellent in color fastness to light and heat resistance and offers awide variety of colors, particularly distinct colors.

Also, oil-soluble dyes and dispersion dyes are used to obtain tonerswith distinct color for color electrophotography and colored resins withtransparency and gloss since they are highly soluble in resin.

Moreover, a toner for color electrophotography incorporating asublimational dye makes it possible to obtain images which are high inboth chromaticity and lightness.

In color electrophotography, to obtain full-color images by superposingtoner images of yellow, magenta and cyan colors, the three subtractiveprimaries, it is necessary for each toner to have a good spectralproperty and transparency for color reproduction. Transparency is alsorequired in toners used for color electrophotography on sheets foroverhead projector (hereinafter referred to as OHP). It should also benoted that these toners are required not to be prone to discoloration,fading or bleeding due to light or heat.

A number of means have been proposed to meet such requirements. Forexample, Japanese Patent Publication Open to Public Inspection Nos.295069/1987, 155555/1987 and 217465/1989 respectively disclose a colortoner incorporating various oil-soluble or dispersion dyes, a magentatoner incorporating a Rhodamine dye, and a magenta toner incorporatingan anthraquinone dispersion dye. Also, color toners with improved lighttransmittance are proposed in Japanese Patent Publication Open to PublicInspection Nos. 52560/1987 and 75645/1987.

With respect to colored resins or colored molded resin members,transparency is often demanded as well as color fastness to light,bleeding resistance and resistance against heat during molding.

Optical color filters needed for television cameras, liquid crystaltelevisions, flat panel displays on computers, etc., must be good inspectral property and transparency.

Examples of red pigments for optical filters include those disclosed inJapanese Patent Publication Open to Public Inspection No. 278569/1989.

Although color filters are often produced by dyeing a dyable film ofgelatin, casein, polyvinyl alcohol, or the like on a transparent resinor glass base plate with a pigment having a given spectral property byprinting, sublimational transfer, etc., it is desirable to color theresin itself from the viewpoint of durability.,

Of such conventional coloring agents, organic pigments often fail tosatisfy the requirement for transparency because they are almostinsoluble in resin. On the other hand, oil-soluble dyes and dispersiondyes are prone to discoloration, fading, and bleeding. As forsublimation dyes, they often show re-sublimation over a long period,which in turn may cause image density reduction or staining; therefore,their application is limited to auxiliary use for the above-mentionedpurposes.

Therefore, none of the toners for color electrophotography, coloredresins, colored molded resin members and color filters which incorporatea conventional coloring agent are said to fully satisfy the essentialrequirements described above.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide a dicyanoimidazolecompound derivative which is good in color fastness to light, heatresistance, spectral property, resin solubility and bleeding resistance.

It is another object of the present invention to provide a magenta tonerfor color electrophotography which offers a good spectral property andtransparency and which permits good color reproduction for full-colorelectrophotography.

It is yet another object of the present invention to provide a coloredresin or colored molded resin member which is good in color fastness tolight, bleeding resistance, heat resistance and transparency.

It is still another object of the present invention to provide a resincolor filter which is good in transparency, spectral property anddurability.

A dicyanoimidazole compound derivative of the present invention isrepresented by the formula [I] given below. ##STR3## wherein R¹ and R²independently represent alkyl group (C₁ -C₁₂), alkoxyalkyl group (C₃-C₁₂), hydroxyalkyl group, β-cyanoethyl group, β-chloroethyl group,aralkyl group or aryl group; X represents a hydrogen atom, lower alkoxygroup, methyl group or halogen atom; Y represents hydrogen atom, methylgroup, methoxy group, formylamino group, alkyl (C₁ -C₈) carbonylaminogroup, alkyl (C₁ -C₈) sulfonylamino group or alkoxy (C₁ -C₈)carbonylamino group; --Q-- represents --(CR₂)_(n) -- wherein nrepresents an integer of 1 to 12 and R independently represents hydrogenatom or alkyl group which may be branched, ##STR4## --CH═CH--, --CH₂CH═CHCH₂ -- or

--CH₂ --CH═CH--.

The magenta toner for color electrophotography of the present inventionincorporates at least one kind of the dicyanoimidazole compoundderivative represented by the formula [I] above as coloring agent.

It is preferable that the magenta toner for color electrophotography ofthe present invention comprise at least a binder resin, a coloring agentand a charge control agent, and that the coloring agent be at least onekind of the dicyanoimidazole compound derivative represented by theformula [I] above and the binder resin and charge control agentdescribed above be substantially colorless.

The colored resin of the present invention incorporates at least onekind of the dicyanoimidazole compound derivative represented by theformula [I] above in solution.

The colored molded resin member of the present invention is dyed with atleast one kind of the dicyanoimidazole compound derivative representedby the formula [I] above.

The resin color filter of the present invention incorporates at leastone kind of the dicyanoimidazole compound derivative represented by theformula [I] above in solution.

Another mode of the resin color filter of the present invention is dyedwith at least one kind of the dicyanoimidazole compound derivativerepresented by the formula [I] above in solution.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a visible-band absorption spectrum of the dicyanoimidazolecompound derivative obtained in Preparation Example 1 (Example Compound1).

FIG. 2 is a visible-band absorption spectrum of the dicyanoimidazolecompound derivative obtained in Preparation Example 2 (Example Compound8).

DETAILED DESCRIPTION OF THE INVENTION

In the formula [I] above, which represents the dicyanoimidazole compoundderivative of the present invention, the alkyl groups (C₁ -C₁₂),alkoxyalkyl groups (C₃ -C₁₂) and hydroxyalkyl groups represented by R¹and R², the lower alkoxy group represented by X, the alkyl (C₁ -C₈)carbonylamino group, alkyl (C₁ -C₈) sulfonylamino group and alkoxy (C₁-C₈) carbonylamino group represented by Y may be branched. Examples ofsuch groups include methyl, ethyl, butyl, isoamyl, octyl, 2-ethylhexyl,nonyl, dodecyl, methoxyethyl, ethoxyethyl, hexyloxyethyl,β-hydroxyethyl, 3-hydroxybutyl, methoxy, ethoxy, isopropoxy, sec-butoxy,ethylcarbonylamino, methylsulfonylamino and ethoxycarbonylamino.

In the formula [I], the aralkyl group and aryl group represented by R¹and R² may be substituted with a phenyl group, halogen atom, lower alkylgroup, lower alkoxy group or another substituent. Examples of sucharalkyl or aryl groups include benzyl, phenylethyl, methylbenzyl,2-(4-fluorophenyl)ethyl, 2-(4-methylphenyl)ethyl, naphthylmethyl,phenyl, methoxyphenyl, tolyl, xylyl, biphenylyl and naphthyl.

An example of the production method for a compound represented by theformula [I] of the present invention is given below.

First, 2-amino-4,5-dicyanoimidazole, represented by the formula (a)##STR5## is diazotized by a standard method, followed by coupling withan aniline represented by the formula (b) ##STR6## wherein X, Y, R¹ andR² have the same definitions as above, to yield a known dicyanoimidazolecompound represented by the formula (c) ##STR7## wherein X, Y, R¹ and R²have the same definitions as above.

Next, the compound of the formula (c) is reacted with any one of thecompounds represented by the formulas (d) through (h) given below in thepresence of potassium carbonate or another neutralizing agent in anorganic solvent (e.g., dimethylformamide, acetone, methyl ethyl ketone)to yield the desired product.

The compound which forms the linkage chain (--Q--) is exemplified by thecompounds represented by the following formulas (d) through (h).

    Z--(CR.sub.2).sub.n --Z                                    (d)

wherein Z represents a halogen atom; n represents an integer of 1 to 12,preferably 2 to 6; R independently represents hydrogen atom or alkylgroup which may be branched. ##STR8## wherein Z has the same definitionas above.

    Z--CH═CH--Z                                            (f)

wherein Z has the same definition as above.

    Z--CH.sub.2 CH═CHCH.sub.2 --Z                          (g)

wherein Z has the same definition as above.

    Z--CH.sub.2 --CH═CH--Z                                 (h)

wherein Z has the same definition as above.

The magenta toner for color electrophotography of the present inventioncontains as a coloring agent at least one kind of the dicyanoimidazolecompound derivative represented by the formula [I] above, and it ispreferable that it incorporate at least a substantially colorless binderresin and charge control agent.

The color toner of the present invention can incorporate almost any oneof the conventional known binder resins for toner. To enhance the effectof the binder resin, there are demands for those properties such astransparency, substantial freedom of color (i.e., absence of color orpresence of a color such that toner images do not undergo tonedeterioration), capability of dissolving the dicyanoimidazole compoundderivative of the present invention, positive or negative chargeabilityas such or by the addition of a charge control agent, fluidity underappropriate heating or pressurizing conditions, and pulverizability.

Examples of resins which can serve well as described above includepolystyrene resin, acryl and acrylic resins, styrene (meth)acrylatecopolymer, and polyester resin. Other usable resins include epoxy resin,polyamide resin, polyvinylal resin, polyethylene resin, polypropyleneresin and polyolefin. These resins may be used singly or in blend ofseveral kinds.

The color toner of the present invention may contain a charge controlagent for the purpose of improving its triboelectrical chargeability.The charge control agent is preferably substantially colorless. Here,"substantially colorless" means the absence of color or a color suchthat toner images do not undergo tone deterioration.

Examples of preferably usable charge control agents include those forimparting negative charge such as metal complexes of aromatico-oxycarboxylic acid, e.g., chromium complex, zinc complex or aluminumcomplex of alkyl-substituted salicylic acid, or chromium complex, zinccomplex or aluminum complex of oxynaphthoic acid, and metal complexes ofaromatic dicarboxylic acid such as chromium complex or zinc complexthereof. Examples of those which impart positive charge includequaternary ammonium compounds and polyamine resin.

To prepare a coloring agent for toner of the present invention, it ispreferable to add a dicyanoimidazole compound derivative represented bythe formula [I] in a ratio of 0.5 to 10 parts by weight, more preferably1 to 5 parts by weight, per 100 parts by weight of binder resin.

The toner of the present invention may incorporate one or more othercoloring agents as long as they do not interfere with the purpose oreffect thereof.

The charge control agent is preferably added in a ratio of 0.1 to 10parts by weight, more preferably 0.5 to 5 parts by weight, per 100 partsby weight of toner resin.

To improve toner quality, it is preferable to internally or externallyadd one or more additives other than the charge control agent, such as afluidity improving agent and image peeling preventing agent.

The magenta toner for color electrophotography of the present inventionis, for example, produced as follows:

A toner of 5 to 20 μm in average particle size can be obtained bythoroughly mixing the dicyanoimidazole compound derivative of thepresent invention, a binder resin, a charge control agent and, ifnecessary, a magnetic material, a fluidizing agent and other additivesusing a ball mill or another mechanical mixer, subsequently kneading themixture in a molten state using a hot kneader such as a heat roll,kneader or extruder, cooling and solidifying the mixture, followed bypulverization and classification.

Other usable methods include the method in which the starting materialis dispersed in a binder resin solution and then spray drying thedispersion, and the polymerizing toner production method in which agiven set of materials are mixed in a monomer for binder resin to yieldan emulsified suspension and then polymerizing it to yield the desiredtoner.

When using the toner of the present invention as a two-componentdeveloper, the toner is used in mixture with carrier powder anddeveloped by the two-component magnetic brush developing process, etc.

Any known carrier can be used. Examples of the carrier include ironpowder, nickel powder, ferrite powder, and glass beads of 50 to 200 μmin particle size, and such materials as coated with acrylate copolymer,styrene-acrylate copolymer, styrene-methacrylate copolymer, siliconresin, polyamide resin, ethylene fluoride resin, or the like.

When using the toner of the present invention as a single-componentdeveloper, a small amount of finely divided magnetic powder of iron,nickel, ferrite or the like is added and dispersed upon preparing thetoner as described above. Examples of developing processes which can beused in this case include contact development and jumping development.

The colored resin of the present invention comprises at least one kindof the dicyanoimidazole compound derivative represented by the formula[I] above in solution, the colored resin constituting resin beingexemplified by thermoplastic resins such as styrene resin, acryl resin,styrene-acryl copolymer, polycarbonate, polyamide, polybutyleneterephthalate, polyethylene, polypropylene and polyacetal, andthermosetting resins such as polyester, polyurethane and phenol resin.Particularly, when using the compound derivative of the presentinvention in combination with styrene resin, acryl resin, styrene-acrylcopolymer or polycarbonate, a colored molded member with excellenttransparency can be obtained.

The colored resin of the present invention can, for example, be producedby kneading in a molten state the compound derivative of the presentinvention, represented by the formula [I]. When using the colored resinfor plastic molding, the compound derivative of the present invention isnormally compounded at 0.1 to 1% by weight to the resin. Molding can beachieved by a known means such as injection molding.

The colored resin of the present invention can be used in combinationwith one or more other coloring agents as long as they do not interferewith the purpose or effect thereof.

The colored molded resin member of the present invention has been dyedwith at least one kind of the dicyanoimidazole compound derivativerepresented by the formula [I], and examples of the resin constitutingsaid colored molded resin member include the same as mentioned for thecolored resin described above.

This colored molded resin member can be obtained by dyeing a moldedresin with the compound derivative of the present invention by transfer,printing, sublimational deposition or other means.

A mode of the resin color filter of the present invention comprises atleast one kind of the dicyanoimidazole compound derivative representedby the formula [I] in solution, and another mode of the resin colorfilter of the present invention has been dyed with at least one kind ofthe dicyanoimidazole compound derivative represented by the formula [I].Examples of the resin constituting these color filters include the sameas mentioned for the colored resin described above.

These color filters of resin can, for example, be produced by the methoddescribed in Japanese Patent Publication Open to Public Inspection No.278569/1989 or another method in accordance therewith. Accordingly,examples of such methods include the method in which a dye is mixed withresin and solvent, followed by kneading to yield an ink, which is thenused to dye a dyeable plastic base plate of polyester, polyamide, acrylresin or the like, the method in which a dye is kneaded in resin,followed by sheet molding, the method in which a synthetic resin film isdyed in a solvent such as ethylene glycol, and the method in which anink composition is applied on paper etc. and dyeing a resin plate bytransfer.

In the colored molded resin member and resin color filter of the presentinvention, other coloring agents can be used in combination, as long asthey do not interfere with the purpose and effect thereof.

EXAMPLES

The present invention is hereinafter described in more detail by meansof the following examples, but these are not to be construed aslimitative on the present invention.

PREPARATION EXAMPLE 1

To 27.2 g of a dicyanoimidazole series monoazo compound [compound (A)]represented by the following formula: ##STR9## 200 ml ofdimethylformamide and 13.6 g of potassium carbonate were added, and thismixture was heated to 60° C. with stirring. Then, 8.3 g of1,3-dibromopropane was dropwise added to the mixture. After heating to85° C., reaction was carried out at the constant temperature for 9hours. The resulting reaction mixture was thereafter cooled to roomtemperature, and 600 ml of methanol was added. The separating crystalproduct was collected by filtration, washed with water and dried toyield 18.5 g of a crude product, which was recrystallized with methylethyl ketone to yield 14 g of the compound shown below (Example Compound1 listed in Table 1 below). This compound had a melting point of 256° to257° C. Its visible-band absorption spectrum is as shown in FIG. 1, witha maximum absorption λ max of 530 nm. In FIGS. 1 and 2, the abscissaindicates wavelength and the ordinate indicates absorbance. Theabsorbance of this Example Compound 1 and Examples Compounds 2 through36 described below was determined in the presence of trichloromethane asthe solvent using model 8451A Diode Array Spectrophotometer (trade name,produced by Hewlett Packard). ##STR10##

PREPARATION EXAMPLE 2

To 20.2 g of the compound represented by the following formula:##STR11## 340 ml of acetone, 8.6 g of potassium carbonate and 6.9 g ofα, α'-dibromo-p-xylene were added, followed by reflux with heating for14 hours. The reaction mixture was cooled to room temperature, and 340ml of water was added. The separating crystal product was collected byfiltration, washed with water and dried to yield 19.4 g of a crudeproduct containing a compound represented by the structural formulagiven below. The obtained crude product was dissolved in hot chloroform,and this solution was filtered with heating in the presence of activatedcharcoal. The resulting filtrate was recrystallized in methanol to yield10.9 g of a purified product of the compound shown below (ExampleCompound 8 listed in Table 1 below). Its melting point was 279° to 280°C. The visible-band absorption spectrum is as shown in FIG. 2, with amaximum absorption λ max of 536 nm. ##STR12##

In accordance with the Preparation Examples 1 and 2 given above, othercompounds specified in Table 1 below (Example Compounds 2 through 7 and9 through 36) were obtained In Table 1, the figures in the column for λmax show the visible absorption maxima of respective Example Compounds.

                                      TABLE 1                                     __________________________________________________________________________     ##STR13##                                                                    Compound                                        λmax                   number                                                                              R.sup.1 R.sup.2 X   Y       Q             (nm)                          __________________________________________________________________________     1    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   CH.sub.3                                                                              (CH.sub.2).sub.3                                                                            530                            2    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   CH.sub.3                                                                               ##STR14##    522                            3    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   CH.sub.3                                                                              (CH.sub.2).sub.6                                                                            514                            4    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   H       (CH.sub.2).sub.4                                                                            520                            5    C.sub.4 H.sub.9                                                                       C.sub.4 H.sub.9                                                                       H   H       (CH.sub.2).sub.4                                                                            526                            6    C.sub.4 H.sub.9                                                                       C.sub.4 H.sub.9                                                                       H   CH.sub.3                                                                              (CH.sub.2).sub.6                                                                            520                            7    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            556                            8    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOCH.sub.3                                                                           ##STR15##    536                            9    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.6                                                                            530                           10    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOCH.sub.3                                                                          CH.sub.2 CHCHCH.sub.2                                                                       550                           11    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.4 Cl                                                                    OCH.sub.3                                                                         NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            538                           12    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.4 CN                                                                    H   NHCOC.sub.2 H.sub.5                                                                   (CH.sub.2).sub.3                                                                            528                           13    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOC.sub.3 H.sub.7                                                                   (CH.sub.2).sub.3                                                                            558                           14    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCHO   (CH.sub.2).sub.3                                                                            546                           15    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOOC.sub.2 H.sub.5                                                                  (CH.sub.2).sub.3                                                                            544                           16    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOC.sub.6 H.sub.13                                                                  (CH.sub.2).sub.3                                                                            540                           17    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHSO.sub.2 CH.sub.3                                                                   (CH.sub.2).sub.3                                                                            558                           18    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHSO.sub.2 C.sub.2 H.sub.5                                                            (CH.sub.2).sub.3                                                                            560                           19                                                                                   ##STR16##                                                                            C.sub.2 H.sub.5                                                                       H   CH.sub.3                                                                              (CH.sub.2).sub.3                                                                            536                           20    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       Cl  H       (CH.sub.2).sub.3                                                                            524                           21    CH.sub.3                                                                              CH.sub.3                                                                              H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            538                           22    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOC(CH.sub.3).sub.3                                                                 (CH.sub.2).sub.3                                                                            542                           23    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.4 OH                                                                    H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            550                           24    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.4 OCH.sub.3                                                             H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            544                           25    C.sub.2 H.sub.4 OCH.sub.3                                                             C.sub.2 H.sub.4 OCH.sub.3                                                             H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            536                           26    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.4 OC.sub.4 H.sub.9                                                      H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            548                           27    C.sub.2 H.sub.5                                                                        ##STR17##                                                                            H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            556                           28    C.sub.4 H.sub.9                                                                        ##STR18##                                                                            H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            558                           29    C.sub.5 H.sub.11                                                                      C.sub.5 H.sub.11                                                                      H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            560                           30    C.sub. 6 H.sub.13                                                                     C.sub.6 H.sub.13                                                                      H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            560                           31    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       OCH.sub.3                                                                         CH.sub.3                                                                              (CH.sub.2).sub.3                                                                            542                           32    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       Cl  NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            544                           33    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                  NHCOCH.sub.3                                                                          (CH.sub.2).sub.6                                                                            548                           34    C.sub.2 H.sub.5                                                                        ##STR19##                                                                            H   NHCOCH.sub.3                                                                          (CH.sub.2).sub.3                                                                            558                           35    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   CH.sub.3                                                                              CH.sub.2 CHCH 534                           36    C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       H   NHCOCH.sub.3                                                                          CHCH          560                           __________________________________________________________________________

The magenta toner for color electrophotography of the present inventionand the actual imaging performance of developers incorporating saidtoner will be explained by means of Examples 1 through 5 below.

EXAMPLE 1

Styrene-acryl copolymer [HIMER TB-100 (trade name), produced by SanyoKasei Co., Ltd.] . . . 100 parts

Example Compound 1 . . . 2 parts

Charge control agent [Bontron E-84 (trade name), produced by OrientChemical Industries Ltd.] . . . 1 part

The above ingredients were uniformly pre-mixed using a high-speed mixer,and the kneaded in a molten state using an extruder, cooled, and roughlymilled with a vibration mill. The obtained coarse product was pulverizedusing an air jet mill equipped with a classifier to obtain fine powderof 5 to 20 μm in particle size. To this powder 1% by weight of colloidalsilica was added to yield a toner.

Five parts of the obtained toner was admixed with 95 parts ofresin-coated iron powder carrier [F813-150 (trade name), produced byNippon Teppun Co., Ltd.] to yield a developer.

This developer was found to be -20.1 μC/g in the amount of initialblowoff charges. The amounts of initial blowoff charges of thisdeveloper under low-temperature low-humidity conditions (5° C., 30%relative humidity) and high-temperature high-humidity conditions (35°C., 90% relative humidity) were -20.3 μC/g and -20.5 μC/g, respectively,indicating very high stability.

When this developer was used for a commercial copying machine (seleniumdrum type) to form toner images, fog-free very distinct magenta colorimages were obtained. Even long term repeated use permitted theobtainment of stable copies free of quality degradation. The obtainedcopies showed a good color fastness to light of grade 7.

Color fastness to light was assessed by applying the sample to a fademeter (carbon arc type) for 40 hours and then comparing with the controlkept in a normal state using a blue scale (Japanese Industrial StandardJIS L0841). The same applies in Examples below.

EXAMPLE 2

Polyester [HP-301. produced by The Nippon Gohsei Kagaku Kogyo K.K.] . .. 100 parts

Example Compound 2 . . . 2 parts

Charge control agent [Bontron E-88 (trade name), produced by OrientChemical Industries Ltd.] . . . 1 part

Lower polypropylene [Biscal 550-P (trade name), produced by Sanyo KaseiCo., Ltd.] . . . 10 parts

The above ingredients were treated in the same manner as in Example 1 toyield a toner. Three parts of the obtained toner was admixed with 97parts of iron powder carrier [TEFV200/300 (trade name), produced byNippon Teppun Co., Ltd.] to yield a developer. This developer was foundto be -22.7 μC/g in the amount of initial blowoff charges.

When copies were taken in the same manner as in Example 1, thisdeveloper gave fog-free distinct magenta images with high thin-linereproducibility. Even long term repeated use permitted the obtainment ofstable copies free of image quality degradation.

This developer was used on a sheet for OHP to form toner images. Thesheet was used for OHP to obtain distinct magenta images on screen.

EXAMPLE 3

Styrene-acryl copolymer [HIMER TB-1000 (trade name), produced by SanyoKasei Co., Ltd.] . . . 100 parts

Example Compound 8 . . . 3 parts

Charge control agent [Bontron E-84 (trade name), produced by OrientChemical Industries Ltd. . . . 1 part

Lower polypropylene [Biscal 550-P (trade name), produced by Sanyo KaseiCo., Ltd.] . . . 10 parts

The above ingredients were treated in the same manner as in Example 1 toyield a toner. Three parts of the obtained toner was admixed with 97parts of iron powder carrier [TEFV200/300 (trade name), produced byNippon Teppun Co., Ltd.] to yield a developer. This developer was foundto be -20.5 μC/g in the amount of initial blowoff charges.

When the developer was used for a commercial color copying machine[produced by Canon Inc.] to take copies, fog-free very distinct magentaimages were obtained. Even long term repeated use permitted theobtainment of stable copies free of image quality degradation. When thisdeveloper was used in combination with a cyan toner and a yellow toner,color images with very good color reproduction were obtained.

EXAMPLE 4

Styrene-acryl copolymer [HIMER TB-1000 (trade name), produced by SanyoKasei Co., Ltd.] . . . 100 parts

Example Compound 10 . . . 2 parts

Charge control agent [Bontron P-51 (trade name), produced by OrientChemical Industries Ltd.] . . . 1 part

Lower polypropylene resin [Biscal 550-P (trade name), produced by SanyoKasei Co., Ltd.] . . . 10 parts

The above ingredients were treated in the same manner as in Example 1 toyield a toner. Three parts of the obtained toner was admixed with 97parts of iron powder carrier [TEFV200/300 (trade name), produced byNippon Teppun Co., Ltd.] to yield a developer. This developer was foundto be +22.2 μC/g in the amount of initial blowoff charges.

When the developer was used for a commercial copying machine [Canon NP(trade name), produced by Canon Inc.] to take copies, fog-free verydistinct magenta images were obtained. Even long term repeated usepermitted the obtainment of stable copies free of image qualitydegradation.

EXAMPLE 5

Styrene-acryl copolymer [HIMER TB-1000 (trade name), produced by SanyoKasei Co.. Ltd.] . . . 100 parts

Example Compound 33 . . . 3 parts

Iron sesquioxide (Fe₂ O₃) . . . 10 parts

Charge control agent [Bontron P-51 (trade name), produced by OrientChemical Industries Ltd.] . . . 1 part

Lower polypropylene [Biscal 550-P (trade name), produced by Sanyo KaseiCo., Ltd.] . . . 10 parts

The above ingredients were uniformly premixed using a ball mill to yielda premix, which was then kneaded in a molten state using a twin-screwextruder [PCM-30 (trade name), produced by Ikegai Seisakusho Co., Ltd.],cooled and thereafter roughly crushed, pulverized and classified toyield a single-component toner of 5 to 15 μm in particle size.

When this toner was used for a commercial copying machine [NP-201 (tradename), produced by Canon Inc.] to form toner images, fog-free magentaimages were obtained with high quality.

COMPARATIVE EXAMPLE 1

A toner was prepared and used to form copied images in the same manneras in Example 1 except that the dicyanoimidazole compound derivativeaccording to the present invention (Example Compound 1) was replacedwith the compound (A) shown in Preparation Example 1. The initiallyobtained copied images had a distinct magenta color, but repeatedcopying for a long period resulted in uneven copying with color densitydegradation and staining. The obtained copies had a color fastness tolight of grade 5, lower by 2 grades than in Example 1.

The colored resin of the present invention will be described in moredetail by means of Examples 6 and 7 below.

EXAMPLE 6

500 g of polystyrene resin [Dialex (trade name), produced by MitsubishiMonsanto Chemical Co.] and 0.25 g of Example Compound 1 as coloringagent were placed in a stainless steel tumbler and mixed thoroughly withstirring for 1 hour. This mixture was kneaded in a molten state at 200°C. using a vent-type extruder and pelletized by a standard method toyield colored pellets.

These pellets were then dried at 80° C. for 3 hours and subsequentlysubjected to an ordinary method of injection molding at a moldingtemperature of 200° C. to prepare a test plate. Example Compound 1 wellendured the heat during kneading in a molten state and molding, giving ared molded plate with excellent transparency.

The color fastness to light of this molded plate was found to be ofgrade 7, and its bleeding resistance was of grade 5.

The bleeding resistance was determined by leaving the test plate at 120°C. for 24 hours while keeping the test plate under a load of 200 g/cm²between two uncolored molded plates of the same material as the testplate, and then evaluating the degree of staining onto the uncoloredmolded plates using a grey scale (Japanese Industrial Standard JISL0805). The same applies in Examples below.

EXAMPLE 7

500 g of methacryl resin [Acrypet (trade name), produced by MitsubishiRayon Co., Ltd.] and 0.25 g of Example Compound 8 as coloring agent wereplaced in a stainless steel tumbler and mixed thoroughly with stirringfor 1 hour. This mixture was kneaded in a molten state at 210° C. usinga vent-type extruder and pelletized by a standard method to yieldcolored pellets. When these pellets were treated in the same manner asin Example 6, Example Compound 8 well endured heat during kneading in amolten state and molding, giving a red molded plate with excellenttransparency. This molded plate was found to be good in color fastnessto light at grade 7 and bleeding resistance at grade 5.

COMPARATIVE EXAMPLE 2

To compare color fastness to light and bleeding resistance, a moldedplate was prepared in the same manner as in Example 6 except thatExample Compound 1 used in Example 6 was replaced with 0.125 g of thecompound (A) shown in Preparation Example 1.

This molded plate was found to be of grade 5 in color fastness to lightand grade 3 or 4 in bleeding resistance, lower by 2 grades and 1 to 2grades, respectively, in comparison with Example 6.

The resin color filter of the present invention will be hereafterdescribed in more detail by means of Examples 8 and 9.

EXAMPLE 8

On a molded plate of methacrylate resin [Acrypet (trade name), producedby Mitsubishi Rayon Co., Ltd.], a sheet of transfer paper, prepared from2 g of Example Compound 1, 10 g of Pyronal MD1200 [(trade name),produced by Toyobo Corporation] and 1 g of silica gel, was placed,followed by calendering at 200° C. to yield a red filter as a result ofdyeing the molded plate.

This filter was found to be of grade 7 in color fastness to light and ofgrade 5 in bleeding resistance. Its spectral transmittance also wasgood.

EXAMPLE 9

5 g of polyester film and 2 g of Example Compound 11 were placed into1000 g of ethylene glycol, and the polyester film was dyed at 120° C.for 90 minutes to yield a red filter. This filter was found to be ofgrade 6 to 7 in color fastness to light and of grade 5 in bleedingresistance. Its spectral transmittance also was good.

COMPARATIVE EXAMPLE 3

To compare color fastness to light and bleeding resistance, a red filterwas prepared in the same manner as in Example 9 except that ExampleCompound 11 used in Example 9 was replaced with 1 g of a monoazocompound represented by the structural formula given below. ##STR20##

This red filter was found to be of grade 5 in color fastness to lightand of grade 3 in bleeding resistance, lower by 1 to 2 grades and 2grades, respectively, in comparison with Example 9.

What is claimed is:
 1. Magenta toner for color electrophotographyincorporating at least one kind of the dicyanoimidazole compound ascoloring agent, said Dicyanoimidazole compound having the formula##STR21## wherein R¹ and R² each independently is alkyl having 1-12carbon atoms, alkoxyalkyl having 3-12 carbon atoms, hydroxy lower alkyl,β-cyanoethyl, β-chloroethyl, aralkyl or aryl, in which said aralkyl andaryl are unsubstituted or substituted with phenyl, halogen, lower alkyland lower alkoxy; X is hydrogen, lower alkoxy, methyl or halogen; Y ishydrogen, methyl, methoxy, formylamino, alkylcarbonylamino having 1-8carbon atoms in the alkyl moiety, alkylsulfonylamino having 1-8 carbonatoms in the alkyl moiety or alkoxycarbonylamino having 1-14 8 carbonatoms in the alkyl moiety; and --Q-- is --(CR₂)_(n) -- in which n is1-12 and each R independently is hydrogen ar alkyl, ##STR22##
 2. Magentatoner for color electrophotography comprising at least a binder resin, acoloring agent, and a charge control effective amount of a chargecontrol agent, wherein at least one kind of dicyanoimidazole compound iscontained as coloring agent and said binder resin and charge controlagent are substantially colorless said Dicyanoimidazole compound havingthe formula ##STR23## wherein R¹ and R² each independently is alkylhaving 1-12 carbon atoms, alkoxyalkyl having 3-12 carbon atoms, hydroxylower alkyl, β-cyanoethyl, β-chloroethyl, aralkyl or aryl, in which saidaralkyl and aryl are unsubstituted or substituted with phenyl, halogen,lower alkyl and lower alkoxy; X is hydrogen, lower alkoxy, methyl orhalogen; Y is hydrogen, methyl, methoxy, formylamino, alkylcarbonylaminohaving 1-8 carbon atoms in the alkyl moiety, alkylsulfonylamino having1-8 carbon atoms in the alkyl moiety or alkoxycarbonylamino having 1-8carbon atoms in the alkyl moiety; and --Q-- is --(CR₂)_(n) -- in which nis 1-12 and each R independently is hydrogen or alkyl, ##STR24## 3.Magenta toner for color electrophotography of claim 2 wherein saidcharge control agent is metal complex of aromatic o-oxycarboxylic acidor metal complex of aromatic dicarboxylic acid.
 4. Magenta toner forcolor electrophotography of claim 2 wherein said charge control agent isone or more kinds of charge control agent which impart negative chargeselected from the group consisting of chromium complex ofalkyl-substituted salicylic acid, zinc complex of alkyl-substitutedsalicylic acid, aluminum complex of alkyl-substituted salicylic acid,chromium complex of oxynaphthoic acid, zinc complex of oxynaphthoicacid, aluminum complex of oxynaphthoic acid, chromium complex ofaromatic dicarboxylic acid and zinc complex of aromatic dicarboxylicacid.
 5. Magenta toner for color electrophotography of claim 2 whereinsaid charge control agent is quaternary ammonium compound of polyamineresin.
 6. Magenta toner for color electrophotography of claim 2 whereinsaid binder resin is one or more kinds of resin selected from the groupconsisting of polystyrene resin, acryl and acrylic resins,styrene-(meth)acrylate copolymer, polyester resin, epoxy resin,polyamide resin, polyvinylal resin, polyethylene resin, polypropyleneresin and polyolefin.
 7. Magenta toner for color electrophotography ofclaim 2 incorporating at least one kind of the dicyanoimidazole compoundderivative of claim 1 as coloring agent and a charge control agent, in aratio of 0.5 to 10 parts by weight and 0.1 to 10 parts by weight,respectively, per 100 parts by weight of binder resin.
 8. Colored resincomprising at least one kind of dicyanoimidazole compound derivative insolution, said Dicyanoimidazole compound having the formula ##STR25##wherein R¹ and R² each independently is alkyl having 1-12 carbon atoms,alkoxyalkyl having 3-12 carbon atoms, hydroxy lower alkyl, β-cyanoethyl,β-chloroethyl, aralkyl or aryl, in which said aralkyl and aryl areunsubstituted or substituted with phenyl, halogen, lower alkyl and loweralkoxy; X is hydrogen, lower alkoxy, methyl or halogen; Y is hydrogen,methyl, methoxy, formylamino, alkylcarbonylamino having 1-8 carbon atomsin the alkyl moiety, alkylsulfonylamino having 1-8 carbon atoms in thealkyl moiety or alkoxycarbonylamino having 1-8 carbon atoms in the alkylmoiety; and --Q-- is --(CR₂)_(n) -- in which n is 1-12 and each Rindependently is hydrogen or alkyl, ##STR26##
 9. Colored resin of claim8 wherein said resin is a thermoplastic resin selected; from the groupconsisting of styrene resin, acryl resin, styrene-acryl copolymer,polycarbonate, polyamide, polybutylene terephthalate, polyethylene,polypropylene and polyacetal.
 10. Colored resin of claim 8 wherein saidresin is a thermosetting resin selected from the group consisting ofpolyester, polyurethane and phenol resin.
 11. Colored resin of claim 8incorporating at least one kind of the dicyanoimidazole compound in aratio of 0.1 to 10% by weight to the resin.
 12. Colored molded resinmember dyed with at least one kind of the dicyanoimidazole compoundderivative of claim
 8. 13. Colored molded resin member of claim 12wherein the resin which constitutes the molded resin member is a resinselected from the group consisting of styrene resin, acryl resin,styrene-acryl copolymer, polycarbonate, polyamide, polybutyleneterephthalate, polyethylene, polypropylene, polyacetal, polyester,polyurethane and phenol resin.
 14. Resin color filter dyed with at leastone kind of the dicyanoimidazole compound derivative of claim 8 insolution.
 15. Resin color filter dyed with at least one kind of thedicyanoimidazole compound derivative of claim
 8. 16. Resin color filterof claim 14 wherein said resin is a resin selected from the groupconsisting of styrene resin, acryl resin, styrene-acryl copolymer,polycarbonate, polyamide, polybutylene terephthalate, polyethylene,polypropylene, polyacetal,l polyester, polyurethane and phenol resin.17. Resin color filter of claim 15 wherein said resin is a resinselected from the group consisting of styrene resin, acryl resin,styrene-acryl copolymer, polycarbonate, polyamide, polybutyleneterephthalate, polyethylene, polypropylene, polyacetal, polyester,polyurethane and phenol resin.